Oakland, FL Homes for Sale

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  $800,000 Open Sat 1AM - 3PM

  • 5 Beds
  • 3 Baths
  • 3,528 Sq Ft

  1970 Standing Rock Cir, Oakland, FL 34787

  Discover expansive living and modern sophistication in this STUNNING 5-bedroom, 3-bath home in the highly desirable Oakland Trails community. Offering over 3,500 SQUARE FEET of beautifully designed space and built in 2019, this residence combines contemporary comfort with UPSCALE UPGRADES—creating a home that truly feels “better than new.” Step inside to an inviting OPEN-CONCEPT LAYOUT, where the

  Jennifer Wemert WEMERT GROUP REALTY LLC

  1970 Standing Rock Cir, Oakland, FL 34787
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  $2,130,760 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,992 Sq Ft

  1146 Prado Ln, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of

  Heather Spirazza REGENCY REAL ESTATE LLC

  1146 Prado Ln, Oakland, FL 34787
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  $2,238,120 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,204 Sq Ft

  1173 Prado Ln, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Sunburst Model by Davila HomesDiscover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautifully designed 4,204-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of

  Alexis Anderson REGENCY REAL ESTATE LLC

  1173 Prado Ln, Oakland, FL 34787
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  $2,995,000 New Construction

  • 6 Beds
  • 6.5 Baths
  • 5,144 Sq Ft

  312 Briley Ave, Oakland, FL 34760

  Under Construction. Introducing an extraordinary luxury estate by Element Home Builders in the sought after Briley Farm community, where timeless design, exceptional craftsmanship, and modern elegance come together on a beautiful oversized, nearly half acre corner lot. This remarkable 6-bedroom, 6.5-bath custom residence offers an unparalleled living experience with every detail thoughtfully

  Carolina Dumit CORCORAN PREMIER REALTY

  312 Briley Ave, Oakland, FL 34760
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  $714,500 Open Sat 12:30PM - 2:30PM

  • 5 Beds
  • 4 Baths
  • 3,163 Sq Ft

  2450 Standing Rock Cir, Oakland, FL 34787

  Come tour this stunning two-story Meritage Home thoughtfully designed for modern living and effortless entertaining! The open-concept floor plan features a spacious kitchen that seamlessly overlooks the living and dining areas, creating a setting for family gatherings or dinner parties. Upstairs, enjoy a versatile loft ideal for movie nights, game days or relaxing with friends. Go outside to your

  Anamaria Marquez PREMIER SOTHEBYS INT'L REALTY

  2450 Standing Rock Cir, Oakland, FL 34787
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  $1,000,000

  • 4 Beds
  • 2 Baths
  • 2,708 Sq Ft

  624 Hull Island Dr, Oakland, FL 34787

  Find out about the unique chance to be the owner of a 2,700 sqft home which sits on 2.55 private acres which we think is the ideal setting for space, privacy, and great growth. This 1983 built home has been very well preserved in it’s original condition which makes it the perfect choice for buyers who are after land, character and the freedom to update the home to suit their own style. In the

  

  Carmelo Nuccio

  RE/MAX EXCLUSIVE COLLECTION

  (321) 449-7661

  624 Hull Island Dr, Oakland, FL 34787
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  $535,000

  • 3 Beds
  • 2.5 Baths
  • 2,014 Sq Ft

  9029 Sonoma Coast Dr, Oakland, FL 34787

  Experience modern Florida living in this stunning, move-in-ready home at 9029 Sonoma Coast Dr, Winter Garden. Built in 2020, this light-filled residence features 3 spacious bedrooms, 2.5 bathrooms, and an open-plan layout that blends comfort with contemporary style, offering over 2,000 square feet of thoughtfully designed living space.? Step inside to discover a beautifully updated interior with

  

  Abraham Mendez

  NONA LEGACY POWERED BY LA ROSA

  (321) 766-5509

  9029 Sonoma Coast Dr, Oakland, FL 34787
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  $849,000

  • 4 Beds
  • 4.5 Baths
  • 2,741 Sq Ft

  3375 Hanging Tide St, Oakland, FL 34787

  An Enchanting Suburban Gem Marries the appeal of small-town life with the allure of urban conveniences. 4 Bedroom, 4.5 Bathroom POOL Home situated within the Gated Community of the stylish Lakeview Preserve on beautiful Johns Lake. Sitting on a private cul-de-sac, this residence offers breathtaking sunset views over the pool and an inviting indoor-outdoor living experience. The heart of the home

  Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

  3375 Hanging Tide St, Oakland, FL 34787
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  $369,895

  • 3 Beds
  • 2.5 Baths
  • 1,592 Sq Ft

  1428 Scarlet Oak Loop, Winter Garden, FL 34787

  NEW - Seller offering $5,000 CREDIT towards NEW CARPET AND PAINT for BUYER! Welcome to 1428 Scarlet Oak Loop, a beautifully updated townhome in one of Winter Garden’s most sought-after gated communities! This well-maintained residence combines comfort, energy efficiency, and modern upgrades throughout. Featuring a brand-new roof, new HVAC system, and spray-foam insulation in the attic, you’ll

  Eric Bress, Jr ERIC BRESS REAL ESTATE LLC

  1428 Scarlet Oak Loop, Winter Garden, FL 34787
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  $709,990 New Construction

  • 5 Beds
  • 4 Baths
  • 3,195 Sq Ft

  2986 Good Vibes Way, Oakland, FL 34787

  Under Construction. Welcome to the Steely, an innovative two-story Next Gen® home. This home features a private suite with a separate entrance, living area, kitchenette, bedroom, bathroom and laundry, ideal for multigenerational households. The main home is host to an inviting open-concept layout that blends the kitchen, living and dining areas, while a luxe owner’s suite at the back of the home

  Ben Goldstein LENNAR REALTY

  2986 Good Vibes Way, Oakland, FL 34787
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  $569,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,175 Sq Ft

  2934 Good Vibes Way, Oakland, FL 34787

  Under Construction. This popular new Hendrix is a four-bedroom home with convenient single-story living. Three secondary bedrooms are located near the front of the home off the foyer, near a versatile flex space ready to be used as an office or studio. An open-concept floorplan blends the kitchen, living and dining areas with easy access to a covered patio, while a luxe owner’s suite is nestled

  Ben Goldstein LENNAR REALTY

  2934 Good Vibes Way, Oakland, FL 34787
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  $607,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,692 Sq Ft

  2930 Good Vibes Way, Oakland, FL 34787

  Under Construction. The Jagger has it all! This sleek new two-story home features a convenient game room on the second level, perfect for entertaining, relaxation and more. The first floor is host to an inviting open-concept layout shared between a modern kitchen, elegant dining room and comfortable family room. Three secondary bedrooms boast a private space near the front of the home off the

  Ben Goldstein LENNAR REALTY

  2930 Good Vibes Way, Oakland, FL 34787
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  $375,000

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft

  507 W Oakland Ave, Oakland, FL 34760

  One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 507 W Oakland Avenue, where comfort, charm, and convenience come together in one perfect location!Nestled in the heart of Oakland, this beautiful home offers one of the most desirable addresses in the area. Enjoy being just steps from the neighborhood park, a mile from the scenic Oakland

  Jennifer Ibarra REAL BROKER, LLC

  507 W Oakland Ave, Oakland, FL 34760
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  $1,850,000

  • 6 Beds
  • 5 Baths
  • 4,104 Sq Ft

  1101 Eagles Pass Way, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two

  Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

  1101 Eagles Pass Way, Oakland, FL 34787
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  $1,700,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 4,171 Sq Ft

  1096 Riverway Dr, Oakland, FL 34787

  Welcome to 1096 Riverway Drive, a fully custom home built by RCB Homes, currently under construction in the award-winning community of Oakland Park. Scheduled for completion in December 2025, this home spans 4,000 square feet of thoughtfully designed living space.Set on a picturesque tree-lined street, the home’s inviting curb appeal is enhanced by a large wrap-around front porch, a long

  Ken Pozek REAL BROKER, LLC

  1096 Riverway Dr, Oakland, FL 34787
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  $499,990 New Construction

  • 4 Beds
  • 3 Baths
  • 1,847 Sq Ft

  4580 Maple Waltz, Oakland, FL 34787

  Exceptional investment opportunity! This stunning new townhome built by Pulte Homes is located in the desirable Park Side Trails community in Clermont, FL. The property is already leased starting November 28th with a 12-month contract at $2,800/month, offering immediate rental income and a great return potential.Featuring a bright and open floor plan with abundant natural light throughout,

  Marta Faustino DTB FLORIDA REALTY, INC.

  4580 Maple Waltz, Oakland, FL 34787
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  $749,000

  • 5 Beds
  • 3 Baths
  • 3,493 Sq Ft

  1751 Standing Rock Cir, Oakland, FL 34787

  Nestled in the highly desirable Oakland Trails community, this beautifully designed 5-bed, 3-bath "Montclair" former model home spans nearly 3,500 square feet of thoughtfully planned living space. The first floor opens with a spacious family room, separate formal living and dining areas, and a fifth bedroom with adjacent bath. The open-concept kitchen boasts an oversized island, double ovens,

  Julie Bettosini STOCKWORTH REALTY GROUP

  1751 Standing Rock Cir, Oakland, FL 34787
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  $545,000

  • 3 Beds
  • 2 Baths
  • 1,513 Sq Ft

  131 Ryan Ct, Oakland, FL 34760

  Discover your next home at 131 Ryan Ct in charming Oakland, FL. This well-maintained 3-bedroom, 2-bathroom house features beautiful wood-look tile floors throughout the entire home. Recent updates make this property move-in ready. The roof was replaced in 2021, followed by a new AC system in 2020, new windows in 2023, and a brand-new water heater in 2024. The kitchen showcases wood cabinets

  

  Deanna Meredith

  LUXE PROPERTIES LLC

  (321) 495-8071

  131 Ryan Ct, Oakland, FL 34760
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  $389,000

  • 2 Beds
  • 2.5 Baths
  • 1,472 Sq Ft

  2218 Gopher Tortoise Terrace, Oakland, FL 34760

  Enjoy low-maintenance living in this beautifully kept 2-bedroom, 2.5-bathroom townhome. The open main level offers seamless flow with plank flooring and thoughtfully designed spaces for everyday living. The kitchen showcases quartz countertops, an upgraded backsplash, stainless steel appliances, and bar seating that opens to the living area. A dedicated nook provides the perfect spot for a home

  Chelsea Eckert CAM REALTY & PROPERTY MANAGEME

  2218 Gopher Tortoise Terrace, Oakland, FL 34760
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  $969,000

  • 4 Beds
  • 4.5 Baths
  • 3,408 Sq Ft

  9988 Beach Port Dr, Oakland, FL 34787

  Welcome to 9988 Beach Port Drive in the beautiful community Waterleigh in Winter Garden! This stunning property offers the perfect blend ofmodern luxury and serene coastal living. This home provides a peaceful retreat that embodies the essence of relaxation and comfort. With itsspacious layout, stylish design, and picturesque surroundings, 9988 Beach Port Driver is truly a gem waiting to

  Yukey Hoo U KEY REALTY

  9988 Beach Port Dr, Oakland, FL 34787
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  $465,000

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  2690 Bobcat Chase Blvd, Oakland, FL 34787

  Love Where You Live — in Longleaf at Oakland! ? Welcome to Longleaf at Oakland, one of Central Florida’s most sought-after communities near Winter Garden, where modern living meets natural serenity. This immaculate 3-bedroom, 2-bath home with a 2-car garage backs to peaceful conservation land—so you’ll enjoy privacy, stunning views, and no rear neighbors. Built in 2019 and cared for like new,

  Marnetta Arnett LPT REALTY, LLC

  2690 Bobcat Chase Blvd, Oakland, FL 34787
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  $75,000

  • Land
  • 0.11 Acre
  • $681,818 per Acre

  121 S Nixon St, Oakland, FL 34760

  If you're looking for land in Oakland, you have certainly found it! Located in the most picturesque neighborhood in central Florida, this beautiful lot could be the site of your next home. Oakland is quaintly situated in between Winter Garden and Clermont, blending small town feel with activity brimming everywhere you turn.

  Ramon Morales SANCTUM REALTY PROFESSIONALS LLC

  121 S Nixon St, Oakland, FL 34760
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  $785,000

  • 4 Beds
  • 3 Baths
  • 2,909 Sq Ft

  9062 Sonoma Coast Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Special Financing Available — Ask for Details!Experience resort-style living in the highly desirable Waterleigh community of Winter Garden. This one-of-a-kind home sits on a rare, oversized lot with no rear neighbors, offering ultimate privacy and tranquility — perfect for families or anyone seeking a private retreat in one of Central Florida’s

  Asher Chen AAA GLOBAL VENTURES PA

  9062 Sonoma Coast Dr, Oakland, FL 34787
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  $1,020,300 New Construction

  • 4 Beds
  • 4 Baths
  • 4,271 Sq Ft

  4608 Golden Birch Ave, Oakland, FL 34787

  Under Construction. Welcome to Parkside Trails! Explore the charm of this premier Clermont location, offering exclusive amenities and quick access to shopping, dining, and entertainment. With a mix of new construction, single-family and townhomes, plus a variety of exclusive amenities, families will love coming home. Now Selling Onsite with 4 Models Open Daily!Introducing the exquisite

  Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  4608 Golden Birch Ave, Oakland, FL 34787
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  $997,790 New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,313 Sq Ft

  4632 Golden Birch Ave, Oakland, FL 34787

  Under Construction. Welcome to Parkside Trails! Explore the charm of this premier Clermont location, offering exclusive amenities and quick access to shopping, dining, and entertainment. With a mix of new construction, single-family and townhomes, plus a variety of exclusive amenities, families will love coming home. Now Selling Onsite with 4 Models Open Daily!Introducing the exquisite

  Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  4632 Golden Birch Ave, Oakland, FL 34787
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  $848,690 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,810 Sq Ft

  5812 Dancing Willow St, Oakland, FL 34787

  Under Construction. Welcome to Parkside Trails! Explore the charm of this premier Clermont location, offering exclusive amenities and quick access to shopping, dining, and entertainment. With a mix of new construction, single-family and townhomes, plus a variety of exclusive amenities, families will love coming home. Now Selling Onsite with 4 Models Open Daily!Step into the Scarlett by Pulte

  Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

  5812 Dancing Willow St, Oakland, FL 34787
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  $670,000

  • 4 Beds
  • 2.5 Baths
  • 2,473 Sq Ft

  2606 Bobcat Chase Blvd, Oakland, FL 34787

  Stunning former MODEL HOME on a premium CORNER lot – loaded with custom upgrades and just footsteps to the community POOL! Welcome to this beautifully appointed and lushly landscaped 4-bedroom, 2.5-bath home filled with high-end designer touches and thoughtful upgrades throughout, offering both comfort and style. Step inside to discover a bright, open floor plan featuring elegant luxury plank

  Ashley Boyd BHHS FLORIDA REALTY

  2606 Bobcat Chase Blvd, Oakland, FL 34787
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  $279,900

  • 3 Beds
  • 2 Baths
  • 1,747 Sq Ft

  651 J W Jones Rd, Winter Garden, FL 34787

  *****Sellers motivated! Sellers will consider closing assistance to Buyer(s).***** Welcome Home! Let the stresses of the day melt away as you step into this beautiful residence in the highly sought-after Winter Garden. Relax on the screened front porch as you soak in the peaceful atmosphere. Inside, the open-concept design makes entertaining effortless, with a spacious living area, a kitchen bar

  David Seeley EXIT REALTY TRI-COUNTY

  651 J W Jones Rd, Winter Garden, FL 34787
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  $475,000

  • Land
  • 0.51 Acre
  • $931,373 per Acre

  17858 Hither Hills Cir, Winter Garden, FL 34787

  Discover the perfect blend of luxury and natural beauty with these stunning lakefront lots in the Lake Apopka Sound subdivision. Set along the shores of scenic Lake Apopka, these spacious homesites offer breathtaking water views, serene sunsets, and access to one of Central Florida’s most picturesque settings.Lake Apopka Sound provides the ideal backdrop for your custom dream home. With

  Chris Kaminski SMART SOLUTIONS REALTY LLC

  17858 Hither Hills Cir, Winter Garden, FL 34787
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  $465,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,730 Sq Ft

  8937 Matriarca Alley, Oakland, FL 34787

  Move in ready! Freshly painted last year in “North Star” inside, and luxury vinyl plank flooring (no carpets) in this end townhouse just minutes away from theme parks and great shopping at Legado community in Windermere. 3 spacious bedrooms, and 2.5 bathrooms combine with generous living space in this 2-story townhome. Designed for entertaining, the "Minneola" features a large gathering room

  Tony Wong, LLC SANCTUM REALTY PROFESSIONALS LLC

  8937 Matriarca Alley, Oakland, FL 34787
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  $995,000

  • 4 Beds
  • 3.5 Baths
  • 2,758 Sq Ft

  8708 Sonoma Coast Dr, Oakland, FL 34787

  Nestled in Phase 3 of Waterleigh in Horizon West, this stunning single-story home offers 4 bedrooms and 3.5 bathrooms on a premium .41-acre lot with no rear neighbors, providing both privacy and tranquility. Situated on a quiet cul-de-sac, the home features beautiful views and a peaceful setting, just a short stroll from a charming community green space with a pavilion and picnic area. Inside,

  Linda Sirois LONDON FOSTER REALTY

  8708 Sonoma Coast Dr, Oakland, FL 34787
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  $630,000

  • 4 Beds
  • 3.5 Baths
  • 2,743 Sq Ft

  12554 Westhaven Oak Dr, Oakland, FL 34787

  This tenant-occupied home, rented for $3,400/month until June 30, 2026, presents an excellent investment opportunity with immediate income. Located in the desirable Osprey Ranch community of Winter Garden, the property features 4 bedrooms, 3.5 bathrooms, and 2,743 heated square feet of living space. The functional floor plan includes a modern kitchen with all appliances and a laundry room with

  Adriana Franzoi WRA BUSINESS & REAL ESTATE

  12554 Westhaven Oak Dr, Oakland, FL 34787
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  $799,135 New Construction

  • 6 Beds
  • 4.5 Baths
  • 3,412 Sq Ft

  15093 Tea Tree Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Anna Maria w/ Bonus, an award-winning open-concept home designed for modern living and effortless entertaining. The thoughtfully designed layout flows seamlessly from the great

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  15093 Tea Tree Dr, Oakland, FL 34787
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  $675,000

  • 4 Beds
  • 3 Baths
  • 2,650 Sq Ft

  529 Johns Landing Way, Oakland, FL 34787

  Welcome to your dream home in a prestigious gated community! This stunning 4-bedroom, 3-bathroom house offers 2,650 square feet of comfortable living space designed for both relaxation and entertainment. The thoughtfully designed layout includes a versatile fourth bedroom that can easily serve as a mother-in-law suite, perfect for multi-generational living or hosting extended guests. The primary

  Denise Pellegrino REAL BROKER, LLC

  529 Johns Landing Way, Oakland, FL 34787
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  /2

  $773,260 New Construction

  • 4 Beds
  • 3 Baths
  • 3,038 Sq Ft

  15075 Tea Tree Dr, Oakland, FL 34787

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Biscayne, a spacious two-story single-family home designed with both style and functionality in mind. The 20-foot ceiling entryway creates a stunning first impression, leading

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  15075 Tea Tree Dr, Oakland, FL 34787
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  $1,050,000

  • 5 Beds
  • 4 Baths
  • 3,084 Sq Ft

  877 Tilden Oaks Trail, Winter Garden, FL 34787

  Modern Craftsman Charmer in Oakland Park – Corner Lot, No Rear Neighbors, and Steps from the West Orange Trail!Welcome to 877 Tilden Oaks Trail, a beautifully designed David Weekley Modern Craftsman home in the heart of Oakland Park—one of Winter Garden’s most sought-after communities. Featuring 5 bedrooms, 4 bathrooms, 3,084 sq. ft., and stunning curb appeal, this move-in ready home offers

  Matthew Matin CLOCK TOWER REALTY

  877 Tilden Oaks Trail, Winter Garden, FL 34787
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  $1,675,000 New Construction

  • 5 Beds
  • 5 Baths
  • 3,895 Sq Ft

  Custom Carrabelle Plan at Oakland Park, Winter Garden, FL 34787

  AR Homes Builder

  884 Tilden Oaks Trail Unit 37615294, Winter Garden, FL 34787
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  /96

  $1,675,000 New Construction

  • 5 Beds
  • 5 Baths
  • 4,819 Sq Ft

  166 Hammock Preserve Loop, Oakland, FL 34787

  AR Homes Builder

  166 Hammock Preserve Loop, Oakland, FL 34787
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  /38

  $399,000

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft

  12043 Holystone St, Oakland, FL 34787

  “The property is currently active for sale but is rented for $2500 monthly, with a lease valid until February 2026. The lease must be honored, so the property is best suited for investors looking for a rental income opportunity.”Welcome to Waterleigh community! This townhome has 3 bedroom 2.5 bathroom is conveniently located in Waterleigh Phase 4, near the Elementary and Middle School! It

  Ruth Santos Blystone WRA BUSINESS & REAL ESTATE

  12043 Holystone St, Oakland, FL 34787
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  /60

  $997,000

  • 5 Beds
  • 3.5 Baths
  • 3,910 Sq Ft

  9549 Bolero Rd, Oakland, FL 34787

  The lakefront life of grandeur awaits you in this stunningly enhanced North Haven model by DR Horton's luxury line, Emerald Homes! Structural enhancements are plentiful and include a Control4 Smart Home Automation System, custom designed closets in nearly every closet throughout the home, security system, technology operated window treatment, entire home water softener, reverse osmosis kitchen

  Jacquelyn Voigt KELLER WILLIAMS REALTY AT THE LAKES

  9549 Bolero Rd, Oakland, FL 34787

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